Ethylene Glycol → 2-(2-Bromoethyl)-2-methyl-1,3-dioxolane

HRID 1106293Notes

Reaction equation

HRID 1106293 reaction equation
[Br:1][CH2:2][CH2:3][C:4](=[O:6])[CH3:5].[CH2:7](O)[CH2:8][OH:9].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.O.C1(C)C=CC=CC=1>[CH2:8]1[O:9][C:4]([CH2:3][CH2:2][Br:1])([CH3:5])[O:6][CH2:7]1

Participants

8

Reactant 4

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 11430Potassium CarbonateHCID 124527344-Bromobutan-2-one

Product 1

HCID 118056192-(2-Bromoethyl)-2-methyl-1,3-dioxolane

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 75 g of 4-bromo-2-butanone, 40 g of ethylene glycol, 250 mg of p-toluenesulfonic acid acid and 500 ml of toluene is refluxed for about 4-6 hours under a Dean-Stark water trap. The mixture is cooled, poured into ethyl acetate and dilute potassium carbonate solution. The organic layer is separated, washed with water, dried over sodium sulfate, stripped of solvent and the residue is distilled under reduced pressure to give the title product.

Workup

  1. temperatureThe mixture is cooled
  2. customThe organic layer is separated
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. distillationthe residue is distilled under reduced pressure

Sources & evidence

ORD record
ord-5579699143fc4414b844206821a3455e
Source dataset
uspto-grants-1982_01
Patent number
US04312994

Reaction notes

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